Synthesis, Characterization and Anti‐inflammatory Activity of 5‐{[((5‐Substituted‐aryl)‐1,3,4‐thiadiazol‐2‐yl)thio]‐n‐alkyl}‐1,3,4‐oxadiazole‐2‐thiol

Abstract

A series of potent and less toxic, 5-{[((5-substituted aryl)-1,3,4-thiadiazol-2-yl) thio]-n-alkyl}-1,3,4-oxadiazole-2-thiol was synthesized. Each compound was evaluated for anti-inflammatory activity by carrageenan-induced rat paw oedema method. Compounds PS1, PS4, PS9, and PS12 showed comparatively potent anti-inflammatory activity as compared to control as well as other test compounds. These potent compounds were also tested for acute ulcerogenic activity. Results of both studies were found statistically significant.

5-(3-Hydroxyphenyl)-1,3,4-oxadiazole-2(3H)-thione hemihydrate

“…Oxadiazoles are an important class of heterocyclic compounds because of their broad biological activities. In particular, 1,3,4-Oxadiazole derivatives are known to act as antibacterial (Ahmed et al, 2018), antimicrobial (Zheng et al, 2018), anticancer (Glomb et al, 2018), anti-inflammatory (Abd-Ellah et al, 2017), analgesic (Husain & Ajmal, 2009), antitubercular (Ali & Shaharyar, 2007;Zampieri et al, 2009), and vasodilatory (Shirote & Bhatia, 2010) agents. They are also important as starting materials for cycloaddition reactions (Vasilev et al, 2007), and are employed in the synthesis of furans (Wolkenberg & Boger, 2002), natural products (Yuan et al, 2005) and plant-growth hormones (Won et al, 2011).…”

Synthesis and Screening of New [1,3,4]Oxadiazole, [1,2,4]Triazole, and [1,2,4]Triazolo[4,3-b][1,2,4]triazole Derivatives as Potential Antitumor Agents on the Colon Carcinoma Cell Line (HCT-116)

“… 13 − 15 We may therefore conclude that 1,3,4-oxadiazole is one of the main pharmacophores that plays an important role in pharmaceutical chemistry and has a broad range of important biological activities including anti-inflammatory, 16 , 17 anticancer, 18 − 21 antimalarial, 22 antibacterial, 23 − 26 anticonvulsant, 27 antitubercular, 28 − 30 anti-allergic agent, 31 analgesic, 32 and vasodilator. 33 Also, the survey showed that the presence of a morpholine ring on a heterocyclic system leads to an enhancement of pharmacological activities in most cases, 34 − 36 where the presence of morpholine in heterocyclic compounds could increase the solubility of these compounds in aqueous solutions because of the formation of a morpholine ammonium salt. 37 Also, Schiff bases derived from different heterocyclic compounds have a broad variety of biological activities.…”

Palladium-Catalyzed Cross-Coupling of 1,3,4-Oxadiazoles and Styrenes: An Efficient Method to Synthesize 2-Alkenyl-1,3,4- Oxadiazoles§

“…3 Several molecules containing the 1,3,4-oxadiazole moiety display a broad range of biological activities, and some of them are used as drugs (Figure 1). Oxadiazoles are known to exhibit antiinflammatory, 4 cytotoxic, 5 antifungal, 6 antianalgesic, 7 anti-HIV, 8 antimalarial, 9 anticancer, 10 antibacterial, 11 vasodilatory, 12 muscle-relaxant, 13 and CNS-depressant activities. 14 In continuation of our work 15 on the synthesis of substituted oxadiazoles, we report a new C-C bond-forming reaction that leads to the synthesis of 2-alkenyl-1,3,4-oxadiazole derivatives.…”